Heretofore, as the production method of 6-halogeno-3-arylpyridine derivative, (1) a method for reacting 2-halo-5-pyridyl boric acid with arylbromide (see: J. Org. Chem., 2002, vol. 67, page 7541); (2) a method reacting 2-chloro-5-bromopyridine with aryl boric acid (see: Heterocycles 1987, vol. 26, page 2711); (3) a method reacting 1,2,4-triazine prepared by the reaction of 2-chloro-5-cyanopyridine and hydrazine, with 2,5-norbornadiene (see: JP-A-2000-355581); (4) a method for chlorinating 5-arylpyridine (see: Chem. Pharm. Bull., 1988 vol. 36, page 2244) or the like are known.
However, in the method of (1) and (2), cryogenic condition is required in preparing a 2-halo-5-pyridyl boric acid or an aryl boric acid, which are raw material. In addition, in the method of (3), multistep reaction is required. And, in the method of (4), isomers having the different position of chlorination are produced as by-product, therefore, there is a problem that the isomers difficult to separate have been formed. Thus, any methods of the above-described (1) to (4) were not the industrially advantageous methods.
In addition, heretofore, as a cross-coupling process between two aromatic compound derivatives, the method for reacting Grignard compound with halogen compound in the presence of palladium compound is known (see: J. Organometallic Chem., 1976, vol. 118, page 349). However, there are few reaction examples in which arylpyridine derivative is synthesized by reacting Grignard compound of pyridine derivative with halogenoaryl derivative. There is known a method for synthesizing 2-arylpyridine derivative by reacting 2-pyridylmagnesium bromide derivative obtained from the reaction of pyridine derivative which is halogenized at 2-position regarded as generally more reactive substitution site and magnesiation reagent, with halogenoaryl derivative (see: J. Molecular Structure, 2000, Vol. 553, page 61). However, there is not known a method for synthesizing 5-pyridylmagnesiumbromide derivative and halogenoaryl derivative by reacting 5-halogenopyridine derivative having a functional group at 2-position with magnesiation reagent.